This application is directed to novel ketoxime carbonates and a method of preparing ketoxime carbonates generally. The ketoxime carbonates of the invention represent valuable intermediates. The process for preparing these compounds provides a route for synthesis of previously unknown substances, substances which are not commercially available and provides an efficient route for the synthesis of materials that were previously only manufacturable with great difficultly. The ketoxime carbonates that may be prepared via this process may be used in one or more of the following Utilities: pesticides, herbicides, pharmaceuticals, as well as, special solvents and intermediates for dyestuffs. See, for example U.S. Pat. No. 3,933,846 to Daum which discloses generally the preparation of benzimidazol-2-yl-carbamic acid alkyl esters. The reference discloses a special embodiment in which a 2-aminobenzimidazole is reacted with a carbonate, like acetone oxime carbonate, and an alkanol to form benzimidazol-2-yl-carbamic acid alkyl esters which are useful as plant protection agents and particularly useful as fungicides and mite ovicides.
Currently, ketoxime carbonates are prepared by reacting a desired ketoxime with phosgene. See, R. G. Kostyanovskii et al., "New Derivatives of Hexafluoroacetone oxime", (Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1615-1619, July, 1974), which discloses the preparation of hexafluoroacetone oxime carbonate by the reaction of hexafluoroacetone oxime with phosgene and pyridine in ether at 20.degree. C. See also, East German patent 61,263 to Jumar et al. in which acetone oxime carbonate is prepared as a by-product in low yield in a process for preparing chloroformyl oximes by reacting a ketoxime with phosgene.
It is an object of this invention to provide new ketoxime carbonates.
It is another object of this invention to provide a novel method for the preparation of ketoxime carbonates.
It is another object of this invention to provide a method of preparing ketoxime carbonates in high yield.